Amide composition



Patented Oct. 31, 1950 AIWIDE COMPOSITION Lewis 0. Gunderson, ParkRidge, 111., assignor to Dearborn Chemical Company, Chicago, 111., acorporation of-Illinois No Drawing. Original application September 9,

1947, Serial No. 773,078. Divided and this application November 24,1947, Serial No. 787,845

4 Claims.

This invention relates to novel amide compositions suitable, inter alia,for use in eliminating foaming conditions in steam boilers.

The novel compositions of the present invention include trilauroyldiethylene triamine, tetralauroyl triethylene tetramine, tetralauroyltetraethylene pentamine and pentacapryl tetraethylene pentamine. Thesecompounds may be used, for instance, to inhibit foaming of boiler water.

It is therefore an important object of the present invention to providenovel amide compositions adapted for use in the prevention of foaming inboiler water and for other purposes.

Other and further features and objects of the present invention willbecome apparent from the following detailed disclosure and appendedclaims.

Trilauroyl diethylene triamine, having the formula:

may be prepared as follows. 75 grams of lauric acid were heated with 12grams diethylene triamine for 6 hours at 180 to 200 C. Titration of thereaction mass with normal alcoholic solution of sodium hydroxide, usingPoirriers Blue as indicator, showed that the reaction mass contained1.4% of unreacted acid. The product is soluble in benzene and ethylacetate and contains 6.65% nitrogen, as compared with the theoreticalnitrogen content of 6.46%.

Tetralauroyl triethylene tetramine, having the formula:

may be prepared as follows. 75 grams of lauric acid were heated with 17grams triethylene tetramine at 180 to 220 C. for 6 hours. Titration ofthe reaction mass with 1% normal alcoholic sodium hydroxide solution,using Poirriers Blue as indicator, showed that reaction mass contained4.8% unreacted acids. The product is soluble in benzene and ethylacetate and contains 7.22% nitrogen, as compared with the theoreticalnitrogen content of 6.73

Tetralauroyl tetraethylene pentamine, having the formula:

HN-CHz-CHa-N-CHrCHz-N-CHr-CHz-N-CHz-CHz-NH (1:0 0:0 0:0 I :=o 3111123lnHzs uHzs 111323 may be prepared as follows. grams lauric acid wereheated with 22 grams tetraethylene pentamine at 180 to 200 C. for 6hours. Titration of the reaction mass with normal alcoholic sodiumhydroxide solution, using Poirriers Blue as indicator, showed thatreaction mass contained 3.27% unreacted acid. The product is soluble inethyl acetate, and contains 7.60% nitrogen, as compared with thetheoretical nitrogen content of 7.60%.

Tetralauroyl tetraethylene pentamine may also be prepared as follows.grams of lauric acid were heated with 19 grams of tetraethylenepentamine at from to C. for 21 hours, yielding a product having an acidnumber of 28.1. The reaction mass obtained had a nitrogen content of7.12%. Correction for the acid content indicates a nitrogen content of7.90%.

Pentacapryl tetraethylene pentamine, having the formula:

I I I I 091119 CQHID 091119 (391110 CuHlt may be prepared as follows.345 grams capric acid, 54 grams tetraethylene pentamine and 20 grams ofdry silica gel were heated together for 30 hours at from 160 to 210 C.Titration of the reaction mass with s normal alcoholic sodium hydroxidesolution, using Poirriers Blue as indicator, showed that 34.4% of theacid had not reacted. The unreacted capric acid was removed by vacuumdistillation, 124.2 grams being recovered. The residue from thedistillation was recrystallized from 300 cc. hot acetone. The insolublematerial which was filtered off weighed 72.9 grams and formed a lightbrown powder melting at 107 to 110 and having a nitrogen content of7.29%, compared with a theoretical nitrogen content of 7.3

Pentacapryl tetraethylene pentamine may also be prepared as follows. 5lbs. of capric acid and 1.1 lb. of tetraethylene pentamine were placedin a 4-liter beaker and heated with constant stirring over a free flameat 190 to 299 C. for 35 hours. [at this time, the free acidity haddropped to 5.56%. The product obtained had a nitrogen content of 8.30%and, corrected for the unreacted acid, a nitrogen content of 7.29%.

The foam inhibiting compositions of the present invention may beintroduced into steam boiler water in the form of colloidal dispersionsthat may be stabilized with tannin, gum arabic, pectin, or the like. Ifdesired, the foam inhibiting compositions may be introduced into theboiler in the form of a solution in an appropriate solvent, such asisopropyl alcohol or the like. The dosages required are generally quitesmall, on the order of some few parts per million of boiler water. Ingeneral, from 0.1 to about 50 parts per million of foam inhibitingcompounds may be added to boiler water, preferably in combination withtannin. Addition of foam inhibiting compounds may be repeated asrequired to prevent foaming.

This application is a division of my application, Serial No. 773,078,filed September 9, 1947.

Many details in composition and procedure may be varied through a widerange without departing from the principles of this invention, and itis, therefore not my purpose to limit the patent granted on thisinvention otherwise than necessitated by the scope of the appendedclaims.

I claim as my invention:

1. As a new composition of matter, a material selected from the groupconsisting of trilauroyl diethylene triamine, tetralauroyl triethylenetetramine, tetralauroyl tetraethylene pentamine, and pentacapryltetraethylene pentamine.

2. As a new composition of matter, pentacapryl tetraethylene pentamine.

3. As a new composition of matter, tetralauroyl tetraethylene pentamlne.

4. As a new composition of matter, tetralauroyl triethylene tetramine.

LEWIS O. GUNDERSON.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 1,534,525 Hartmann et a1. Apr.21, 1925 2,243,329 DeGroote et al May 27, 1941 2,322,201 Jayn et a1 June15, 1943 2,345,632 Robinson et a1 Apr. 4, 1944 2,371,736 Carson Mar. 20,1945 2,419,404 Johnson Apr. 22, 1947

1. AS A NEW COMPOSITION OF MATTER, A MATERIAL SELECTED FROM THE GROUPCONSISTING OF TRIAUROYL DIETHYLENE TRIAMINE, TETRALAUROYL TRIETHYLENETETRAMINE, TETRALAUROYL TETRAETHYLENE PENTAMINE, AND PENTACAPRYLTETRAETHYLENE PENTAMINE.